Zirconium Triflate Catalyzed Direct Coupling Reaction of Lactams with Heterocyclic Arenes under Atmospheric Oxygen

Tsuchimoto, Teruhisa; Ozawa, Yoshitaka; Negoro, Ryoju; Shirakawa, Eiji; Kawakami, Yusuke

doi:10.1002/ange.200460429

Cited by 14 publications

(1 citation statement)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…halogenation or any other disposable functionality) 2. Simple and practical methods that eliminate this prerequisite in synthetic design are rare 4…”

Section: Methodsmentioning

confidence: 99%

Direct Coupling of Pyrroles with Carbonyl Compounds: Short Enantioselective Synthesis of (S)‐Ketorolac

2005

View full text Add to dashboard Cite

Nicht aktivierte C(sp2)‐ und C(sp3)‐Atome werden bei der beschriebenen Kupplung von Pyrrolen mit Carbonylverbindungen (Ketonen, Amiden, Estern, Lactonen, Lactamen) verknüpft (siehe Schema). Eine intramolekulare Variante dieser neuen Methode machte den nichtsteroidalen entzündungshemmenden Wirkstoff (S)‐Ketorolac in einer kurzen enantioselektiven Synthese zugänglich. Zudem werden Überlegungen zum Mechanismus dieser Reaktion vorgestellt.

show abstract

“…halogenation or any other disposable functionality) 2. Simple and practical methods that eliminate this prerequisite in synthetic design are rare 4…”

Section: Methodsmentioning

confidence: 99%

Direct Coupling of Pyrroles with Carbonyl Compounds: Short Enantioselective Synthesis of (S)‐Ketorolac

2005

View full text Add to dashboard Cite

show abstract

Chiral Phosphoric Acid‐Catalyzed Enantioselective Aza‐Friedel–Crafts Alkylation of Indoles with γ‐Hydroxy‐γ‐lactams

Courant

Kumarn

et al. 2013

Adv Synth Catal

View full text Add to dashboard Cite

An enantioselective aza-Friedel-Crafts reaction of indoles with g-hydroxy-g-lactams using a chiral phosphoric acid catalyst is reported. The approach described herein provides an efficient access to 5-indolylpyrrolidinones in good to quantitative yields and excellent enantioselectivities (up to > 99% ee). The results suggest that the reaction may proceed via N-acyliminium intermediates associated with the chiral phosphoric acid anion.

show abstract

Alkynylboranes: A Practical Approach by Zinc‐Catalyzed Dehydrogenative Coupling of Terminal Alkynes with 1,8‐Naphthalenediaminatoborane

et al. 2014

View full text Add to dashboard Cite

Under zinc Lewis acid catalysis, terminal alkynes coupled dehydrogenatively with 1,8‐naphthalenediaminatoborane [HB(dan)]. It is important to note that the resulting alkynylboranes with an C(sp)B(dan) bond are isolable by column chromatography on silica gel (SiO2) and are usable as coupling partners for palladium‐ and copper‐catalyzed cross‐coupling reactions with (hetero)aryl halides.magnified image

show abstract

Zirconium Triflate Catalyzed Direct Coupling Reaction of Lactams with Heterocyclic Arenes under Atmospheric Oxygen

Cited by 14 publications

References 24 publications

Direct Coupling of Pyrroles with Carbonyl Compounds: Short Enantioselective Synthesis of (S)‐Ketorolac

Direct Coupling of Pyrroles with Carbonyl Compounds: Short Enantioselective Synthesis of (S)‐Ketorolac

Chiral Phosphoric Acid‐Catalyzed Enantioselective Aza‐Friedel–Crafts Alkylation of Indoles with γ‐Hydroxy‐γ‐lactams

Alkynylboranes: A Practical Approach by Zinc‐Catalyzed Dehydrogenative Coupling of Terminal Alkynes with 1,8‐Naphthalenediaminatoborane

Contact Info

Product

Resources

About